Bromine → Methyl 4-(bromomethyl)-2-hydroxybenzoate

HRID 349689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349689
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][C:8]([CH3:11])=[CH:9][CH:10]=1)[OH:6].[Br:13]Br>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][C:8]([CH2:11][Br:13])=[CH:9][CH:10]=1)[OH:6]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Produkt 1

HCID 22556059Methyl 4-(bromomethyl)-2-hydroxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

A refluxing solution of 4-methylsalicylic acid methyl ester (5.1 g, 31.3 mmol) in carbon tetrachloride (50 mL) was treated dropwise with a solution of bromine (1.6 mL, 31.3 mmol) in carbon tetrachloride (5 mL) while under illumination by a 200 W incandescent light bulb. The reaction mixture was stirred for an additional 30 min at reflux and concentrated in vacuo. The residue was dissolved in EtOAc (50 mL) and washed with aqueous sodium thiosulfate (5%, 50 mL), water (50 mL), and brine (50 mL). The organic layer was dried over Na2SO4, concentrated, and the product 4-bromomethylsalicylic acid methyl ester was isolated by recrystallization from heptane (1.6 g, 21%).

Aufarbeitung

  1. temperatureat reflux
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (50 mL)
  4. washwashed with aqueous sodium thiosulfate (5%, 50 mL), water (50 mL), and brine (50 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5a79f9a8d15349b4994e3c091e7af1f3
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179912B2

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